Avobenzone (BioDeep_00000398992)

   

natural product


代谢物信息卡片


Avobenzone (Parsol 1789)

化学式: C20H22O3 (310.15688620000003)
中文名称: 1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮
谱图信息: 最多检出来源 Helianthus annuus(natural_products) 66.67%

分子结构信息

SMILES: C1=C(C=CC(=C1)C(CC(C2=CC=C(C=C2)C(C)(C)C)=O)=O)OC
InChI: InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3

描述信息

D020011 - Protective Agents > D011837 - Radiation-Protective Agents > D013473 - Sunscreening Agents
C1892 - Chemopreventive Agent > C851 - Sunscreen
D003879 - Dermatologic Agents
D003358 - Cosmetics

同义名列表

2 个代谢物同义名

Avobenzone; Avobenzone (Parsol 1789)



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Nageswara R Pilli, Suresh Narayanasamy, Jeffry Florian, Robbert Zusterzeel, Vikram Patel, David G Strauss, Murali K Matta. Novel simultaneous method for the determination of avobenzone and oxybenzone in human plasma by UHPLC-MS/MS with phospholipid removal pretreatment: An application to a sunscreen clinical trial. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Apr; 1169(?):122615. doi: 10.1016/j.jchromb.2021.122615. [PMID: 33706185]
  • Jeayoung C Shin, Eunyoung Lee, Seungchan An, Sun Hee Jin, Jaehyoun Ha, Won Jun Choi, Minsoo Noh. Benzophenone-3 and benzophenone-8 exhibit obesogenic activity via peroxisome proliferator-activated receptor γ pathway. Toxicology in vitro : an international journal published in association with BIBRA. 2020 Sep; 67(?):104886. doi: 10.1016/j.tiv.2020.104886. [PMID: 32407875]
  • Xin Zhong, Craig A Downs, Yuting Li, Zishan Zhang, Yiman Li, Binbin Liu, Huiyuan Gao, Qingming Li. Comparison of toxicological effects of oxybenzone, avobenzone, octocrylene, and octinoxate sunscreen ingredients on cucumber plants (Cucumis sativus L.). The Science of the total environment. 2020 Apr; 714(?):136879. doi: 10.1016/j.scitotenv.2020.136879. [PMID: 32018996]
  • Murali K Matta, Jeffry Florian, Robbert Zusterzeel, Nageswara R Pilli, Vikram Patel, Donna A Volpe, Yang Yang, Luke Oh, Edward Bashaw, Issam Zineh, Carlos Sanabria, Sarah Kemp, Anthony Godfrey, Steven Adah, Sergio Coelho, Jian Wang, Lesley-Anne Furlong, Charles Ganley, Theresa Michele, David G Strauss. Effect of Sunscreen Application on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial. JAMA. 2020 01; 323(3):256-267. doi: 10.1001/jama.2019.20747. [PMID: 31961417]
  • Julia Hiller, Katrin Klotz, Sebastian Meyer, Wolfgang Uter, Kerstin Hof, Annette Greiner, Thomas Göen, Hans Drexler. Systemic availability of lipophilic organic UV filters through dermal sunscreen exposure. Environment international. 2019 11; 132(?):105068. doi: 10.1016/j.envint.2019.105068. [PMID: 31470219]
  • Katrin Klotz, Kerstin Hof, Julia Hiller, Thomas Göen, Hans Drexler. Quantification of prominent organic UV filters and their metabolites in human urine and plasma samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Sep; 1125(?):121706. doi: 10.1016/j.jchromb.2019.06.033. [PMID: 31302475]
  • Sungjin Ahn, Seungchan An, Moonyoung Lee, Eunyoung Lee, Jeong Joo Pyo, Jeong Hyeon Kim, Min Won Ki, Sun Hee Jin, Jaehyoun Ha, Minsoo Noh. A long-wave UVA filter avobenzone induces obesogenic phenotypes in normal human epidermal keratinocytes and mesenchymal stem cells. Archives of toxicology. 2019 07; 93(7):1903-1915. doi: 10.1007/s00204-019-02462-1. [PMID: 31016361]
  • Murali K Matta, Robbert Zusterzeel, Nageswara R Pilli, Vikram Patel, Donna A Volpe, Jeffry Florian, Luke Oh, Edward Bashaw, Issam Zineh, Carlos Sanabria, Sarah Kemp, Anthony Godfrey, Steven Adah, Sergio Coelho, Jian Wang, Lesley-Anne Furlong, Charles Ganley, Theresa Michele, David G Strauss. Effect of Sunscreen Application Under Maximal Use Conditions on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial. JAMA. 2019 06; 321(21):2082-2091. doi: 10.1001/jama.2019.5586. [PMID: 31058986]
  • Soo In Yang, Shuanghui Liu, Geoffrey J Brooks, Yves Lanctot, James V Gruber. Reliable and simple spectrophotometric determination of sun protection factor: A case study using organic UV filter-based sunscreen products. Journal of cosmetic dermatology. 2018 Jun; 17(3):518-522. doi: 10.1111/jocd.12390. [PMID: 28834040]
  • Binni Ma, Guanghua Lu, Jianchao Liu, Zhenhua Yan, Haohan Yang, Ting Pan. Bioconcentration and multi-biomarkers of organic UV filters (BM-DBM and OD-PABA) in crucian carp. Ecotoxicology and environmental safety. 2017 Jul; 141(?):178-187. doi: 10.1016/j.ecoenv.2017.03.034. [PMID: 28343007]
  • Shigenobu Yoshida, Syuntaro Hiradate, Motoo Koitabashi, Tsunashi Kamo, Seiya Tsushima. Phyllosphere Methylobacterium bacteria contain UVA-absorbing compounds. Journal of photochemistry and photobiology. B, Biology. 2017 Feb; 167(?):168-175. doi: 10.1016/j.jphotobiol.2016.12.019. [PMID: 28068611]
  • Min Gi Kim, Tae Hwan Kim, Beom Soo Shin, Min Gyu Kim, Su Hyun Seok, Kyu-Bong Kim, Jong Bong Lee, Hyeon Gwan Choi, Young Sung Lee, Sun Dong Yoo. A sensitive LC-ESI-MS/MS method for the quantification of avobenzone in rat plasma and skin layers: Application to a topical administration study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Oct; 1003(?):41-6. doi: 10.1016/j.jchromb.2015.09.014. [PMID: 26409261]
  • Valentina Trotta, Filipa Goios, Helena Monteiro, Isabel F Almeida, Santo Scalia. Influence of lipid microparticle encapsulation on in vitro efficacy, photostability and water resistance of the sunscreen agents, octyl methoxycinnamate and butyl methoxydibenzoylmethane. Drug development and industrial pharmacy. 2014 Sep; 40(9):1233-9. doi: 10.3109/03639045.2013.814062. [PMID: 23837520]
  • Gabriela Niculae, Ioana Lacatusu, Nicoleta Badea, Raluca Stan, Bogdan Stefan Vasile, Aurelia Meghea. Rice bran and raspberry seed oil-based nanocarriers with self-antioxidative properties as safe photoprotective formulations. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2014 Apr; 13(4):703-16. doi: 10.1039/c3pp50290b. [PMID: 24590004]
  • Gabriela Niculae, Nicoleta Badea, Aurelia Meghea, Ovidiu Oprea, Ioana Lacatusu. Coencapsulation of butyl-methoxydibenzoylmethane and octocrylene into lipid nanocarriers: UV performance, photostability and in vitro release. Photochemistry and photobiology. 2013 Sep; 89(5):1085-94. doi: 10.1111/php.12117. [PMID: 23789784]
  • Jun-Jen Liu, Sami Nazzal, Tzu-Shan Chang, Tsuimin Tsai. Preparation and characterization of cosmeceutical liposomes loaded with avobenzone and arbutin. Journal of cosmetic science. 2013 Jan; 64(1):9-17. doi: ". [PMID: 23449127]
  • G Niculae, I Lacatusu, N Badea, A Meghea. Lipid nanoparticles based on butyl-methoxydibenzoylmethane: in vitro UVA blocking effect. Nanotechnology. 2012 Aug; 23(31):315704. doi: 10.1088/0957-4484/23/31/315704. [PMID: 22797534]
  • Woan-Ruoh Lee, Shing-Chuan Shen, Saleh A Al-Suwayeh, Yi-Ching Li, Jia-You Fang. Erbium:YAG laser resurfacing increases skin permeability and the risk of excessive absorption of antibiotics and sunscreens: the influence of skin recovery on drug absorption. Toxicology letters. 2012 Jun; 211(2):150-8. doi: 10.1016/j.toxlet.2012.03.797. [PMID: 22483991]
  • Rachel Haywood, Arsen Volkov, Carima Andrady, Robert Sayer. Measuring sunscreen protection against solar-simulated radiation-induced structural radical damage to skin using ESR/spin trapping: development of an ex vivo test method. Free radical research. 2012 Mar; 46(3):265-75. doi: 10.3109/10715762.2011.651719. [PMID: 22236285]
  • Mireia Marin, Virginie Lhiaubet-Vallet, Cecilia Paris, Minoru Yamaji, Miguel Angel Miranda. Photochemical and photophysical properties of dibenzoylmethane derivatives within protein. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2011 Sep; 10(9):1474-9. doi: 10.1039/c1pp05072a. [PMID: 21547313]
  • L Montenegro, M G Sarpietro, S Ottimo, G Puglisi, F Castelli. Differential scanning calorimetry studies on sunscreen loaded solid lipid nanoparticles prepared by the phase inversion temperature method. International journal of pharmaceutics. 2011 Aug; 415(1-2):301-6. doi: 10.1016/j.ijpharm.2011.05.076. [PMID: 21679757]
  • Radava R Korać, Kapil M Khambholja. Potential of herbs in skin protection from ultraviolet radiation. Pharmacognosy reviews. 2011 Jul; 5(10):164-73. doi: 10.4103/0973-7847.91114. [PMID: 22279374]
  • Howard A Epstein. The next frontier of sunscreen protection: beyond sunscreens. Skinmed. 2011 Jul; 9(4):247-50. doi: ". [PMID: 21980710]
  • Santo Scalia, Gilberto Coppi, Valentina Iannuccelli. Microencapsulation of a cyclodextrin complex of the UV filter, butyl methoxydibenzoylmethane: in vivo skin penetration studies. Journal of pharmaceutical and biomedical analysis. 2011 Jan; 54(2):345-50. doi: 10.1016/j.jpba.2010.09.018. [PMID: 20934293]
  • S Scalia, M Mezzena, D Ramaccini. Encapsulation of the UV filters ethylhexyl methoxycinnamate and butyl methoxydibenzoylmethane in lipid microparticles: effect on in vivo human skin permeation. Skin pharmacology and physiology. 2011; 24(4):182-9. doi: 10.1159/000324054. [PMID: 21336009]
  • Beatrice Albertini, Matteo Mezzena, Nadia Passerini, Lorenzo Rodriguez, Santo Scalia. Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone. Journal of pharmaceutical sciences. 2009 Aug; 98(8):2759-69. doi: 10.1002/jps.21636. [PMID: 19067396]
  • Santo Scalia, Matteo Mezzena. Co-loading of a photostabilizer with the sunscreen agent, butyl methoxydibenzoylmethane in solid lipid microparticles. Drug development and industrial pharmacy. 2009 Feb; 35(2):192-8. doi: 10.1080/03639040802244300. [PMID: 18785040]
  • Santo Scalia, Matteo Mezzena. Incorporation in lipid microparticles of the UVA filter, butyl methoxydibenzoylmethane combined with the UVB filter, octocrylene: effect on photostability. AAPS PharmSciTech. 2009; 10(2):384-90. doi: 10.1208/s12249-009-9217-2. [PMID: 19381836]
  • V Iannuccelli, G Coppi, S Sergi, M Mezzena, S Scalia. In vivo and in vitro skin permeation of butyl methoxydibenzoylmethane from lipospheres. Skin pharmacology and physiology. 2008; 21(1):30-8. doi: 10.1159/000109656. [PMID: 17934329]
  • Santo Scalia, Rosanna Tursilli, Nicoletta Sala, Valentina Iannuccelli. Encapsulation in lipospheres of the complex between butyl methoxydibenzoylmethane and hydroxypropyl-beta-cyclodextrin. International journal of pharmaceutics. 2006 Aug; 320(1-2):79-85. doi: 10.1016/j.ijpharm.2006.04.008. [PMID: 16713145]
  • Valentina Iannuccelli, Nicoletta Sala, Rosanna Tursilli, Gilberto Coppi, Santo Scalia. Influence of liposphere preparation on butyl-methoxydibenzoylmethane photostability. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2006 Jun; 63(2):140-5. doi: 10.1016/j.ejpb.2006.01.007. [PMID: 16531026]
  • Elisabetta Damiani, Luca Rosati, Riccardo Castagna, Patricia Carloni, Lucedio Greci. Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation. Journal of photochemistry and photobiology. B, Biology. 2006 Mar; 82(3):204-13. doi: 10.1016/j.jphotobiol.2005.03.011. [PMID: 16442301]
  • Tatiana Armeni, Elisabetta Damiani, Maurizio Battino, Lucedio Greci, Giovanni Principato. Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes. Toxicology. 2004 Oct; 203(1-3):165-78. doi: 10.1016/j.tox.2004.06.008. [PMID: 15363592]
  • Fiorenza Rancan, Stefania Rosan, Kirsten Boehm, Ernesto Fernández, M Eliana Hidalgo, Wanda Quihot, Cecilia Rubio, Fritz Boehm, Helmut Piazena, Ute Oltmanns. Protection against UVB irradiation by natural filters extracted from lichens. Journal of photochemistry and photobiology. B, Biology. 2002 Nov; 68(2-3):133-9. doi: 10.1016/s1011-1344(02)00362-7. [PMID: 12468208]
  • Elisabetta Damiani, Riccardo Castagna, Lucedio Greci. The effects of derivatives of the nitroxide tempol on UVA-mediated in vitro lipid and protein oxidation. Free radical biology & medicine. 2002 Jul; 33(1):128-36. doi: 10.1016/s0891-5849(02)00876-6. [PMID: 12086690]
  • Gerald J Smith, Ian J Miller, John F Clare, Brian L Diffey. The effect of UV absorbing sunscreens on the reflectance and the consequent protection of skin. Photochemistry and photobiology. 2002 Feb; 75(2):122-5. doi: 10.1562/0031-8655(2002)075<0122:teouas>2.0.co;2. [PMID: 11883599]
  • E Damiani, P Carloni, C Biondi, L Greci. Increased oxidative modification of albumin when illuminated in vitro in the presence of a common sunscreen ingredient: protection by nitroxide radicals. Free radical biology & medicine. 2000 Jan; 28(2):193-201. doi: 10.1016/s0891-5849(99)00221-x. [PMID: 11281286]
  • R Jiang, C G Hayden, R J Prankerd, M S Roberts, H A Benson. High-performance liquid chromatographic assay for common sunscreening agents in cosmetic products, bovine serum albumin solution and human plasma. Journal of chromatography. B, Biomedical applications. 1996 Jun; 682(1):137-45. doi: 10.1016/0378-4347(96)00063-1. [PMID: 8832434]